When we look at the current NHL there are only seven teams north of the border while the remaining 24 (soon to be 25) in the states, its always possible that none of the seven Canadian based teams qualify for the playoffs, but t most it's always either two or three teams that do end up making it. However on this COVID shortened season with the US-Canadian border still closed to non-essential travel, the league had to do a massive division realignment. Typically there is one of the three divisions always has seven teams in it. That division is typically the Central Division in the NHL. This year all the Canadian teams were squeezed into one division. The Toronto Maple Leafs, Montreal Canadiens, Ottawa Senators, Winnipeg Jets, Edmonton Oilers, Calgary Flames, and the Vancouver Canucks were scheduled to play 56-games, all within their respected parts of the country. Obviously Toronto, Montreal and Ottawa see each other multiple times a year given the fact that they play in the same division, however they only play the other four teams twice a year. The Jets play the Oilers, Flames and Canucks at least three times a year, while Edmonton, Calgary and Vancouver play each other at least four times each.
This season the Canadian aka the Tim Hortons North Division will send four teams to the postseason, and one of those teams will end up as one of the final four teams standing when it comes to trying to capture the Stanley Cup, which should be awarded at some point this summer. But in a non-COVID World, the NHL regular season would've been 82-games and the divisions wouldn't be realigned, would there actually be four Canadian teams in the playoffs? Looking at the records compared to other teams, absolutely not.
When take a 31 NHL teams, return them into their normal divisions, of the seven Canadian based teams in the NHL, only three of them would actually qualify for the playoffs this season based on their current records. Right now in the current division alignment, the Maple Leafs, Oilers, jets and Canadiens would all be playoff bound. If we put all teams back in their usual 82-game divisions, the Canadians would actually miss out on the playoffs as they would finish well behind the Bruins for the 2nd wild card and final playoff spot in the Eastern Conference.
Since the NHL wants to keep the Stanley Cup Playoffs to the traditional 16-team playoff structure, each division is sending the top four teams in the division. That's why Montreal is in the playoff field, compared to being on the outside looking in in a normal season. Plus in a non-COVID related world, the playoffs would've have started already and we would most likely be wrapping up the first round of the playoffs or beginning the second round of the playoffs.
However, this probably the beat chance for a team north of the border to bring home the Stanley Cup. The last team to win the Cup were the Montreal Canadiens back in 1993 when they defeated the Los Angeles Kings. Since then only four of the seven teams have gone to the Cup Final, but only to lose to an American franchise. The Vancouver Canucks are still the last Canadian based team to reach the Stanley Cup Final, where they lost to the Boston Bruins in 2011. The last team Canadian based team to get to a Conference Final were the Winnipeg Jets in 2018 where they lost to the Vegas Golden Knights. The only other Canadian teams to reach the Cup Final were the Flames in 2004 where they lost to the Tampa Bay Lightning, the Oilers in 2006 where they lost to the Carolina Hurricanes and then the Senators in 2007 where they lost to the Anaheim Ducks.
Of the four Canadian based franchises that will most likely compete for the playoffs, the best chance a team up north has a chance of winning it are the Toronto Maple Leafs, if they can put their playoff demons behind them once and for all. The Maple Leafs haven't been to the second round of the playoffs since 2004. Fair to say it has been a while for them since Toronto has gone on a true run. In three of the last four of Toronto's playoff appearances, they have been eliminated by the Bruins, most notably in 2013 when they blew a 4-1 lead in Game 7 in Boston and lose 5-4 in overtime.
Here is where all seven Canadian based NHL franchises are placed if they were in their normal divisions (Bold indicates Canadian team):
Atlantic: Panthers-69 pts; Lightning- 68 pts; Maple Leafs- 65 pts; Bruins- 62 pts; Canadiens- 51 pts; Red Wings- 43 pts; Senators- 40 pts; Sabres- 33 pts.
Metropolitan: Hurricanes- 71 pts; Capitals- 68 pts; Penguins- 67 pts; NY Islanders- 63 pts; NY Rangers- 58 pts; Flyers- 51 pts; Blue Jackets- 42 pts; Devils- 37 pts
Central: Avalanche- 66 pts; Wild- 65 pts; Jets- 57 pts; Predators- 56 pts; Stars- 54 pts; Blackhawks- 49 pts; Blues- 48 pts;
Pacific: Golden Knights- 70 pts; Oilers- 58 pts: Coyotes- 47 pts; Flames- 45 pts: Sharks- 43 pts; Kings- 42 pts; Canucks- 41 pts; Ducks- 35 pts.
Two things standout, one; the NHL's Pacific Division is atrocious (good omen for the Kraken) two; in a normal setting, the Maple Leafs, Oilers and Jets will all still qualify for the playoffs, looking at where they are placed in their divisions and picture where they would sit in the conference. The Canadiens are the odd man out given how many points they have accumulated to this point and other teams they typically face in the Eastern Conference.
In a normal playoff structure (instituted in 2014): Teams that finish in the top three of their divisions will qualify for the playoffs and then two wild card teams in each conference round out the final four "at large" spots. Here's how the playoff match-ups would look in a non-COVID setting (Canadian teams in bold): East: Hurricanes vs Islanders; Capitals vs Penguins; Panthers vs Bruins; Lightning vs Maple Leafs. West: Golden Knights vs Stars; Oilers vs Coyotes; Avalanche vs Predators; Wild vs Jets. These playoff match-up s are detrermined based on point percentage in each division and where in the standings the team stand. 1 vs 4, 2 vs 3.
Obviously anything can happen in the Stanley Cup Playoffs once they get underway on at some point in late May. The playoffs were supposed to begin on May 11th, however due to COVID issues from multiple teams, the Playoffs have yet to have an official start date.
Once the playoffs f]=get underway, it all depends in a Canadian based franchise can run the table. No Canadian NHL team has hoisted the Cup since the Montreal Canadiens back in 1993.